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To manage multiple ecosystem services (ES) effectively, it is essential to understand how the dynamics of ES maintain healthy ecosystems to avoid potential negative impacts on human well-being in the context of sustainable development. In particular, the Ionian Islands in the central Mediterranean are characterized by high natural, ecological, and recreational value; however, the intensification of human activities over time has resulted in the loss of natural ecosystems, which might have negatively impacted ES. Here, we aimed to assess and understand the spatiotemporal dynamics of ES supply and how these components interact across the Ionian Islands to optimize future ES provision and mitigate current trade-offs. We quantified multiple ecosystem services and analyzed their interactions at a temporal scale across the four prefectures of the Ionian Islands. Seven ES were quantified covering all three ES sections (provisioning, regulating and maintenance, and cultural) of the Common International Classification of Ecosystem Services (CICES). ES interactions were investigated by analyzing ES relationships, identifying ES bundles (sets of ES that repeatedly occur together across space and time), and specifying ES occurrence within bundles. The three ES groups exhibited similar patterns on some islands, but differed on islands with areas of high recreation in parallel to low provisioning and regulating ES. Temporal variations showed both stability and changes to the supply of ES, as well as in the interactions among them. Different patterns among the islands were caused by the degree of mixing between natural vegetation and olive orchards. This study identified seven ES bundles that had distinct compositions and magnitudes, with both unique and common bundles being found among the islands. The olive grove bundle delivered the most ES, while the non-vegetated bundle delivered negligible amounts of ES. Spatial and temporal variation in ES appear to be determined by agriculture, land abandonment, and increasing tourism, as well as the occurrence of fires. Knowledge about the spatial dynamics and interactions among ES could provide information for stakeholders and decision-making processes to develop appropriate sustainable management of the ecosystems on the Ionian Islands to secure ecological, social, and economic resilience.